The biosynthesis of quinazoline alkaloids of Peganum harmala L.

doi:10.1016/S0031-9422(00)85628-9

Phytochemistry

Volume 7, Issue 8, August 1968, Pages 1299-1306

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Abstract

Controlled isolation and purification methods have shown vasicinone and desoxyvasicinone to be natural products. Administration of precursors in vivo has led to the incorporation of ornithine, putrescine and to a lesser degree tryptophan into the alkaloid skeleton. The significance of these findings is discussed.

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Cited by (21)

Quinazoline Alkaloids
1986, Alkaloids: Chemistry and Pharmacology
This chapter describes the simple substituted quinazolin-4-ones, the pyrroloquinazolines, the pyrido[2,1-b]quinazolines, the indoloquinazolines, biosynthesis, and biological activity of quinazoline alkaloids and their analogs. Febrifugine is perhaps one of the most interesting quinazoline alkaloids. Both glomerin and homoglomerin have been isolated as crystalline components from the defensive secretion of the glomerid millipede Glorneris marginatu.¹H-NMR spectra of both alkaloids show the presence of four aromatic protons. The new alkaloids vasicoline, vasicolinone, and adhatodine and anisotine are found only in young plants of Adhatoda vasica in very low yield. The isolation of pure vasicoline and adhatodine is difficult, because both bases are oxidized to vasicolinone and anisotine by atmospheric oxygen. Anthranilic acid (N-methylated where necessary), ammonia or amine, and formic acid or phenylacetic acid derived from phenylalanine units or their equivalents build up the simple substituted quinazoline derivatives. Vasicine is reported to be a bronchodilator, a respiratory stimulant, and hypotensive in action. Its activity against histamine-induced bronchospasm is specific but brief.
Tricyclic Compounds with a Central Pyrimidine Ring and One Bridgehead Nitrogen
1986, Advances in Heterocyclic Chemistry
Tricyclic compounds with a central pyrimidine ring and one bridgehead nitrogen can be divided into three types—angular annelated ring systems, angular annelated ring systems, and linearly annelated ring systems. This chapter describes these three ring systems and discusses the syntheses, reactions, physicochemical properties, and their utilization. Tricyclic compounds containing a three-membered ring including azirino [1,2-c]quinazolines (ring system type I), angular annelated ring systems with nitrogen in the ring angle (type II), and azirino[2,1-b]quinazolines (ring system type III) are discussed. The synthesis, reactions, physicochemical properties, and applications of other angular annelated ring systems with nitrogen away from the ring angle (type I) and nitrogen in the ring angle (type II) are also discussed. The chapter also illustrates the synthesis of linearly annelated tricycles. One of the most widely used synthetic methods for preparation of the linearly annelated tricycles, containing a six-membered aromatic ring A, is the cyclocondensation of anthranilic acids and lactim ethers.
The simple β-carboline alkaloids
1980, Phytochemistry
Zur biosynthese des pyrrolidinringes in peganin
1972, Phytochemistry
Labelled compounds were fed to young plants of Adhatoda vasica in order to clarify the origin of the 'non-anthranilic acid' portion of vasicine (I). Randomly-labelled I was isolated after administration of α-hydroxy-γ-aminobutyric acid-4-¹⁴C. The evidence indicates that C-3 and C-10 of I are derived from a C₂-unit; the specific incorporation of N-acetyl-2′-¹⁴C-anthranilic acid-¹⁵N strongly supports this view.
Glucosylation of solasodine by extracts from Solanum laciniatum
1971, Phytochemistry
The C-27 nitrogenous steroid solasodine has been shown to be an intermediate in the synthesis of the glycoalkaloids solamargine and solasonine by Solanum laciniatum. Administration of solasodine-¹⁴C to excised plant stems led to the isolation of labelled glycoalkaloids and an enzyme preparation catalyzed the conversion of solasodine to the 3β-glucoside with UDP-glucose acting as donor in the reaction.
Biosynthesis of quinazoline alkaloids of Peganum harmala
1971, Phytochemistry
Evidence has been found supporting the proposal that synthesis of vasicine in Peganum harmala occurs from anthranilic acid and a compound closely related to ornithine. Specificity of incorporation of varying degree was observed after feeding glutamic acid-5-¹⁴C, proline-5-¹⁴C, ornithine-2-¹⁴C and -5-¹⁴C, and putrescine-1,4-¹⁴C. The approximately equal distribution of label between C-1 and C-10 of vasicine showed a symmetrical intermediate to be involved in the biosynthetic pathway. Catabolism of tryptophan to anthranilic acid was demonstrated by the specific incorporation of tryptophan [benzene ring-¹⁴C(U)] into vasicine. Experiments designed to examine interconversions between the quinazoline alkaloids were unsuccessful due to the rapid synthesis and degradation of these compounds within the plant.

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The biosynthesis of quinazoline alkaloids of Peganum harmala L.

Abstract

Planta Med.

Zh. Obshch. Khim.

Chem. Abs.

Ann. Chem.

Arch. Pharm.

Experientia

Abhandl. Deut. Akad. Wiss. Berlin Kl. Chem. Geol. Biol.